Hugh Roe O’Donnell, the chief of Tyrconnell, was tearing Connacht up for fun at times during the late 1590’s. In the early years of the war, O’Donnell proved himself capable again and again, leading raids deeper and deeper into English territory, outmanoeuvring any force sent to stop him and generally making a mockery of the crown administration in the area. His allies in the province, such as the O’Rourke’s and the MacDermots, swelled the Tyrconnell army measurably and it was a frequent thing for the English to have next to nothing in response. In comparison, the Lord President of Connacht Conyers Clifford, based in Athlone, was popular enough with the people of the province but had no great martial reputation in Ireland to speak of. He was lacking troops and supplies, operating in unsuitable terrain. His allies among the native Irish were unreliable at best, and many had deserted to the rebel side after the Yellow Ford. While Tyrconnell does not seem to have had the strength to defeat the English totally in the last years of the 16th century, it is fair to say that he was dominant.

Of those native Irish who were allied to the English, the most prominent were the O’Connor’s of Sligo, but even they had been left vastly reduced by the predations of Hugh Roe. Of their formerly substantial estates, now only one fortification – the castle at Collooney – remained in their power. In truth, O’Connor and his men were deemed of more use to Essex in Munster, but even their involvement there could not turn that campaign into more of a success.

Essex wanted the situation in Connacht to change to his advantage. While preparing a thrust against Hugh O’Neill in the north-east, he instructed Clifford, now backed up by reinforcements from the new army sent over from England, to advance north and re-capture the territory and fortifications that Hugh Roe had conquered in the previous years, especially at Sligo. That area was the gateway into Tyrconnell itself, and Essex hoped any offensive move in that direction would at least weaken the overall power of the Ulster rebels.

Essex furthered ordered a naval element to be dispatched from Galway to land behind the rebel-held positions, furthering tightening the noose, and for materials to be made available for a new castle to be built in the area once secured. Such a limited strategy was not exactly the order of the day, but Essex seems to have recognised that a frontal assault would be pointless and that a garrisoning policy was preferable. In that, he was not far off the strategy of later English leaders.

But while Essex and Clifford were drawing up their plans, O’Donnell decided to launch his own strike. In the height of summer 1599, he and a force of 2’000 or so besieged the castle at Collooney, with O’Connor inside it. O’Connor had no means of escape or martial resistance, but the castle was a strong, sturdy fortification, that Hugh Roe had no means of getting into. But, with the weather right and an advantage in men, he was willing to try the option of starvation.

Upon learning of the siege and the peril that one of their strongest native allies now found himself in, Essex had no choice but to order Clifford northwards as soon as possible, with the goal of relieving the siege along with his other responsibilities. Clifford had 1’500 infantry and 200 horse, and moved towards Collooney as fast as he could. Clifford had some military experience, but suffered from a rash streak that Essex apparently warned him about. The resulting combat illustrates a man who was not in full grasp of the situation and was far too impetuous for his own good.

O’Donnell heard of the English force heading his way, his network of intelligence being considerable for the day. Perhaps Hugh Roe always wanted such a confrontation and the siege was just his way to get it. Whether he was prepared for it or not, he quickly enacted a new plan. Leaving 300 men under his cousin Niall Garbh to continue the siege of Collooney and 600 to prevent a naval leading near Sligo (intelligence network again), he moved south-east, joining up with the forces of local allies to increase his own army to its original size. Knowing the road that Clifford would have to march through, he was able to pick his preferred ambush point.

The Curlew Mountains, in County Roscommon today, are a small set of peaks not too far from the town of Boyle. At a hilly pass through these mountains, Hugh Roe laid his trap, creating obstacles from felled trees and arranging his troops to his liking: missile and musket troops up front on the sides of the road, with melee armed infantry hidden behind the ridge of the mountain.

This was in mid-August and the weather was very hot from accounts. Clifford’s troops, on a long march from Athlone and still moving deep into the afternoon of the 15th of August, must have been tired, hungry and thirsty. They should have camped for the night instead of trying the pass, giving themselves a chance to rest and recuperate, or perhaps stayed in Boyle, but Clifford pressed on. It has been suggested that he was operating on bad intelligence regards the mountains defences (having expected an ambush) and wanted to force a passage while there were no enemy troops lying in wait. As such, it was most likely an exhausted army that started through the pass of the Curlew Mountains that afternoon.

The men they were facing were anything but, and well warned about the approach of the enemy force. Gunfire broke out when the English vanguard approached the first barricade, with spears and pikes also being used. The fight here was brief, as the Irish fired and ran almost immediately. The English, perhaps buoyed by this apparent retreat, and expecting this to be the limit of Irish resistance, pressed on up the hill.

The road was badly kept, in boggy ground, with thick forest on one side, severely limiting English options of manoeuvre. As the vanguard advanced, they came in contact with more and more Irish troops from the left and right, receiving a hail of arrows, spears and shot. A firefight of around an hour and a half resulted. It was the English, worse supplied then their opponents, who got into trouble first, running out of ammunition, and then nerve.

The English vanguard, suddenly lacking the ability to fire back at a well-defended enemy, started to break, with the vanguard retreating into the centre group, creating a situation of confusion and panic. The death of van commander Alexander Radcliffe, while he was trying to marshal his forces, must have made matters worse.

With the English clearly in much distress, the Irish infantry were ordered into the fray, appearing from behind the hills and charging into the enemy at speed. The hand to hand fighting must have been brutal. Clifford, after apparently being absent from the battle up to this point, dove into the fray and tried to re-exert his command, but to no avail. While we don’t know how exactly it happened, he fell in this melee, perhaps by a pike to the gut, or a gunshot to the chest.

The English army, now totally disorganised, began to rout back to Boyle. With the arrival of Irish reinforcements belonging to Brian O’Rourke, the pursuit of them could well have turned into a slaughter that may have surpassed the Yellow Ford. However, the commander of the English cavalry, Griffin Markham, had enough sense to lead a charge against the Irish lines, through incredibly dangerous terrain, to break up the attack and buy the retreating infantry time. He had his arm broken for his trouble in this brave act, but his sudden charge probably averted a total disaster. One Irish source excuses the lack of pursuit by simply saying that there were too many fleeing to cut down.

The English made it back to Boyle, and safety, with O’Donnell not interested in further pursuit. The number of English dead is hard to know, estimated by various sources from 120 to 500. It was probably closer to the higher number, judging on the situation.

O’Donnell did not actually take part in the fight, with subordinates like Brian O’Rourke apparently doing most of the actual commanding on the ground. Hugh Roe, for whatever reason, stayed to the rear. His latest victory has been put down by Irish sources to divine intervention from the virgin Mary (this battle does have a lot of religious language attached to it, more so than others), but was more up to his correct positioning of his forces, the way Clifford marched his troops into a bad situation and the typical English underestimation of the Irish.

Clifford was decapitated after death, his head taken to Collooney as a message to the besieged O’Connor. Realising that no relief was coming, he surrendered the castle and further agreed to join the rebellion against the English. It had always been a fickle alliance. Similarly, the naval element of the expedition was aborted, the fleet and its leaders uninterested in pushing the issue.

The Battle of the Curlew Pass was not a defeat on the same lines as Glenmalure or the Yellow Ford, but it was still a defeat, another example of effective Irish troops outperforming supposedly superior English counterparts. It was more lives thrown away recklessly, more propaganda for the rebels, who saw a marked increase in recruitment afterward, especially from Irish soldiers previously finding employment with the English. More and more, the constant march of victories was making the Tyrconnell/Tyrone alliance seem like a viable option for allegiance. The territorial effects of Curlew Pass, with the turning of O’Connor and complete Tyrconnell dominance in North Connacht, was just as important as the actual results of the battle itself. It also led to the creation of a rather compelling remembrance on the site of the battle, the “Gaelic Chieftain”, one of the few such monuments to the Nine Years War in Ireland today.

The battle added to the woes of Essex in Dublin, and was seized upon as another example of his incompetence by enemies back home. Such affairs empowered the push for him to advance an expedition northwards to face Hugh O’Neill, from which he got only his own downfall and eventual death.

We’ve come to a critical point in the Nine Years War. Up to now, it really does seem to have been one rebel success after another, with poor English military leaders blundering to defeat over and over and over again. The rebels, as the 17th century dawned, were in a strong position.

This only makes everything that occurred afterward more interesting of course. Certainly, the fortunes of war seemed to have favoured the Irish, and while it is important to recognise their own strengths and martial ability, we must too recognise the foolishness of the English in regards tactics, supply and knowledge of terrain. It might be fair to say that the Irish got lucky numerous times.

The English only needed to be lucky once. And their luck would slowly start to change, beginning with the next entry.

To read the rest of the entries in this series, click here to go to the index.